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Here’s How to Spend a Relaxing Weekend in Rhinebeck


The historic Hudson Valley town packs boutique shopping, gourmet eats, and cultural to-dos in just a few square blocks in Dutchess County.

Long before cities like Beacon and Hudson lured New York City weekenders and out-of-towners, Rhinebeck served as the go-to Hudson Valley retreat. These days, the riverside spot is as charming as ever, with its abundance of boutique shops, manicured sidewalks, and on-trend restaurants.

Regardless of whether you visit on the regular or have never stepped foot into town before, make this the year you take advantage of all that Rhinebeck has to offer. Try our guide first, then make your own when you plan a return trip — which you will.

9:30 a.m. – Start the day on a sweet note at Samuel’s

Every day, without fail, locals and visitors alike flock to Samuel’s Sweet Shop for coffee, candy, and confections. The spot serves Toby’s Estate Brooklyn coffee to balance out the sugar-centric menu. Pair your caffeine with a fresh apple turnover, muffin, or any other pastry on offer that morning. If you happen to pick up a bit of candy while you’re there, we don’t blame you.

42 E Market St

Sun-Thurs 7:30 a.m. – 8 p.m., Fri-Sat 7:30 a.m. – 9:30 p.m.

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10:30 a.m. – Explore Wilderstein Historic Site

Located in the heart of the Hudson Valley, Wilderstein Historic Site charms with its Queen Anne style design and expansive grounds. On select dates throughout the year, visitors can tour the mansion and explore the vintage treasures that the Suckley family amassed during their three generations inside the house. Outside, 40 acres of manicured gardens and grasses call to hikers and walkers.

330 Morton Rd

Open daily, 9 a.m. – 4 p.m.

12 p.m. – Eat farm-to-table with a twist at The Amsterdam

The Amsterdam brings European flavor to Hudson Valley cuisine in the heart of Rhinebeck. Open for lunch and dinner, The Amsterdam delights with tapas style bites like a roasted carrots with yogurt and pistachios, vegan eggplant toast, and smoked salmon tartine.

6380 Mill St

Lunch: Mon-Fri 12-2:30 p.m.
Dinner: Mon-Thurs 5-9:30 p.m., Fri, Sat 5:30-9:30 p.m., Sun 5:30-9 p.m.

1:30 p.m. – Fly high at the Old Rhinebeck Aerodrome

If you visit Rhinebeck over the weekend, don’t leave without making a trip to the Aerodrome on a Saturday or Sunday afternoon. That’s when the airshows, the high-flying spectacles with historic planes and skilled pilots, take place. Biplane rides are available both before and after the shows, and the museum is open daily.

9 Norton Rd

Museum open daily, May 1 – Oct 31, 10 a.m. – 5 p.m.

Always a thrill to see our books on display… #bookstores @oblongbooks

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4 p.m. – Shop and stroll along Market and Mill

When it comes to shopping, Rhinebeck is a dream destination. With quaint boutiques lining the picturesque Market and Mill Streets, it is all too easy to lose track of time as you hop from one storefront to the next.  For a truly unique experience, head to A.L. Stickle or Oblong Books & Music. They’re the perfect places to find a one-of-a-kind gift or the knickknack you never knew you needed.

Roasted Veggies & Hummus. Healthy eating never tasted better. #springmenu #eatyourveggies

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6:30 p.m. – Dine in style at Terrapin

As the winner of not one, but two Readers’ Picks in our 2017 Best of Hudson Valley Awards, Terrapin is a required stop on any successful trip to Rhinebeck. For a more casual meal, head to the Red Bistro, where you can munch on Hudson Valley Cattle Company hamburgers, BBQ duck quesadillas, and artichoke and ricotta ravioli. On fancier occasions, make a reservation for the Dining Room, where you can savor Hudson Valley cheese plates, blue cheese crusted filet mignon, and seasonal fruit crisp.

6426 Montgomery Rd

Red Bistro: 11:30 a.m. – midnight
Dining Room: Sun-Thurs 5-9 p.m., Fri-Sat 5-9:30 p.m.

8 p.m. – Get a drink, and a history lesson, at Liberty Public House

Instead of letting its historical origins fall to the wayside, Liberty embraces them wholeheartedly. The 1860 Starr Institute building plasters its walls with vintage prints and Americana memorabilia. Take it all in over a cheeky cocktail or Hudson Valley beer. Try the Diplomatic Immunity, with rum, Luxardo maraschino liquor, pineapple juice, and lime, or just opt for a good old Mother’s Milk from Keegan Ales.

6417 Montgomery St

Sun-Thurs 11 a.m. – 9 p.m., Fri-Sat 11 a.m. – 10 p.m.

9 p.m. – Call it a night at the Olde Rhinebeck Inn

With a circa 1745 start date, the Olde Rhinebeck Inn is a true Hudson Valley gem. The American farmhouse offers up a number of country chic rooms that are so cozy you will seriously consider moving in for good. The real seller, however, is the communal breakfast. Overnight guests can energize for the day with treats like French pear pancakes, herb baked eggs, and herb frittatas. Yes, they are as delicious as they sound.

340 Wurtemburg Rd

Did we miss a spot? Let us know where to go to find the best of Rhinebeck in the comments or by email at edit@hvmag.com.

Related: The Best Way to Explore Millbrook